How to shape a drawing to an object (like a city skyline)

Okay, hope I titled this thread properly… I have an image of a city skyline and outdoor speakers that I drew. What I am trying to accomplish is I would like to shape the speaker(s) to the skyline of the city. I've attached an image showing what I mean

I know I will need multiple speakers, I am curious how someone would go about tackling something like this? Is this an ideal image to use? I thank you in advance for your input…